Reversible Z-E isomerism and pharmaceutical implications for SU5416

Drug Development and Industrial Pharmacy

Volumn 31, Issue 10, 2005, Pages 1001-1007

  Sistla, Anand ^a,c   Shenoy, Narmada ^b  

^a PFIZER INC   (United States)

^b AraVasc Inc   (United States)

^c NONE   (United States)

Author keywords

Pharmaceutical implications; Photo isomerism; SU5416; Thermal reversion; Z E isomerism

Indexed keywords

ANGIOGENESIS INHIBITOR; SEMAXANIB; SU 5886; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; DRUG DETERMINATION; DRUG FORMULATION; DRUG QUALITY; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; ISOMERISM; LIGHT EXPOSURE; STRUCTURE ANALYSIS;

ALGORITHMS; ANGIOGENESIS INHIBITORS; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EXCIPIENTS; HALF-LIFE; HUMANS; INDOLES; ISOMERISM; KINETICS; PLASMA; PYRROLES; QUALITY CONTROL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 28744454447     PISSN: 03639045     EISSN: 15205762     Source Type: Journal    
DOI: 10.1080/03639040500306260     Document Type: Article

References (18)

1. Abdel-Mottaleb, M. S. A., Abdel-Kader, M. H., & El-Araby, S. T. (1983). Correlation of the quantum yield of photochemical trans/cis isomerization of some dyestuffs with their electronic structure and with solvent polarity scales. Photochemistry and Photobiology, Proceedings of the International Conference, 2, 1329-1335.
2. Autrey, R. L., & Tahk, F. C. (1967). The synthesis and stereochemistry of some isatylideneacetic acid derivatives. Tetrahedron, 23, 901-917.
3. Becker, H., Sorensen, H., & Sandros, K. (1986). Photochemical isomerization and dimerization of 1-(9-anthryl)-2-nitroehtylene. Journal of Organic Chemistry, 51, 3223-3226.
4. Belsky, I., Dodiuk, H., & Shvo, Y. (1977). Thermal isomerization of heterofulvenes. Dynamic Nuclear Magnetic Resonance Study. Journal of Organic Chemistry, 42, 2734-2741.
5. Benniston, A. C., & Harriman, A. (1994). Photoinduced and thermal isomerization processes for bis-oxonols: rotor volume, stereochemical and viscosity effects. Journal of the Chemical Society, Faraday Transactions, 90(18), 2627-2634.
6. Bramham, J., & Samuel, C. J. (1989). Thermal E- to Z-isomerization of E, Z-cyclo-octa-1,3-diene. Journal of the Chemical Society, Chemical Communications, 1, 29-30.
7. Clarke, L. F., Fiona, O. S., & Hegarty, A. F. (1991). Photoisomerization of (E)- to (Z)-N.N-dimethylhydrazones and thermal reversion. Journal of the Chemical Society, Perkin Transactions, 2, 1559-1652.
8. Fong, T. A., Shawver, L. K., Sun, L., Tang, C., App, H., Powell, T. J., Kim, Y. H., Schreck, R., Wang, X., Risau, W., Ullrich, A., Hirth, K. P., & McMahon, G. (1999). SU5416 is a potent and selective inhibitor of the vascular endothelial growth factor receptor (Flk-1/KDR) that inhibits tyrosine kinase catalysis, tumor vascularization, and growth of multiple tumor types. Cancer Research, 59(1), 99-106.
9. Gille, K., Knoll, H., & Quitzsch, K. (1999). Rate constants of the thermal cis-trans isomerism of azobenzene dyes in solvents, acetone/water mixtures, and in microheterogeneous surfactant solutions. International Journal of Chemical Kinetics, 31, 337-350.
10. Kropp, P. J. (1979). Photochemistry of alkenes in solution. Organic Photochemistry, 4, 1-142.
11. 1H NMR spectroscopy. Magnetic Resonance in Chemistry, 30, 1153-1157.
12. Nakagawa, C. S., & Sigal, P. (1970). Photochemistry of aromatic olefins. I. Photochemical cis-trans isomerization of 1-phenyl-2-butene. Journal of Chemical Physics, 52(6), 3277-3282.
13. Pappalardo, R. R., Marcos, E. S., Ruiz-Lopez, M. F., Rinaldi, D., & Rivail, J. L. (1993). Solvent effects on molecular geometries and isomerization processes: a study of push-pull ethylenes in solution. Journal of the American Chemical Society, 115, 3722-3730.
14. Saltiel, J., Wang, S., Ko, D., & Gormin, D. A. (1998). Cis-trans photoisomerization of the 1,6-diphenyl-1,35,-hexatrienes in the triplet state. The quantum chain mechanism and the structure of the triplet state. Journal of Physical Chemistry, 102, 5383-5392.
15. Turro, N. J. (1969). Mechanisms of sensitized photochemical cis-trans isomerization in solution. Photochemistry and Photobiology, 9, 555-563.
16. Wang, R., & Knoll, H. (2001). Rate constants of the thermal cis-trans isomerism of azo dyes as kinetic probes in aqueous solutions of poly (ethylene glycols) and poly (ethylene oxide)-poly (propylene oxide)-poly (ethylene oxide) block copolymer F88. Langmuir, 17(10), 2907-2912.
17. Whitesides, G. M., Goe, G. L., & Cope, A. C. (1969). Irradiation of cis, cis-1,5-cyclooctadiene in the presence of copper (I) chloride. Journal of the American Chemical Society, 91(10), 2608-2616.
18. Zhang, L., Borysenko, C. W., Albright, T. A., Bittner, E. R., & Lee, T. R. (2001). The cis-trans isomerization of 1,2,5,6-tetrasilacycloocta-3, 7-dienes: analysis by mechanistic probes and density functional theory. Journal of Organic Chemistry, 66(16), 5275-5283.